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Regio- and Stereocontrolled Synthesis of (Z)-α-(Phenylseleno)sulfinyl and -sulfonyl Alkenes via Sulfenic Acids, and a Study of their Reactivity

✍ Scribed by Maria Chiara Aversa; Anna Barattucci; Paola Bonaccorsi; Andrea Temperini

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
316 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A general procedure for the synthesis of α‐(phenylseleno)sulfinyl and ‐sulfonyl alkenes has been described. 1‐(Phenylseleno)ethenyl sulfoxides were prepared by the syn‐addition of in situ‐generated sulfenic acids on to the triple bond of suitably substituted (phenylseleno)acetylenes. 1‐(Phenylseleninyl)ethenyl sulfones were obtained by further oxidation of their sulfinyl analogues. The mild conditions of the sulfenic acid/(phenylseleno)alkyne syn‐addition and its stereospecificity and regioselectivity allowed us to obtain electron‐poor alkenes with a well defined stereochemistry and sensitive substituents at the double bond. Chiral (Z)‐1‐[(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl)sulfinyl]‐1‐(phenylseleno)‐1‐hexene was also obtained via the enantiopure2,3,4,6‐tetra‐O‐acetylglucosulfenic acid. The reactivity of α‐(phenylseleninyl)sulfinyl and ‐sulfonyl alkenes has been evaluated in nucleophilic additions to the electron‐poor double bond, conducted with hard nucleophiles such as piperidine and phenol.

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